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Cell viscosity fluorescence probe and preparation and application of cell viscosity fluorescence probe

A fluorescent probe and viscosity technology, applied in fluorescence/phosphorescence, preparation of organic compounds, luminescent materials, etc., can solve problems such as unreported, and achieve the effects of low cytotoxicity, broad application prospects, and simple synthesis methods

Inactive Publication Date: 2017-07-28
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, probes for detecting viscosity using the up-conversion imaging properties of dyes have not been reported in domestic and foreign journals and patents.

Method used

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  • Cell viscosity fluorescence probe and preparation and application of cell viscosity fluorescence probe
  • Cell viscosity fluorescence probe and preparation and application of cell viscosity fluorescence probe
  • Cell viscosity fluorescence probe and preparation and application of cell viscosity fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Synthesis of fluorescent probe BNCPO.

[0025] Dissolve 1 mmol of cyclopentanone in 15 mL of absolute ethanol, add a small amount of solid NaOH, and stir the reaction solution at room temperature until NaOH is completely dissolved. Then, 2 mmol of 4-dimethylaminophenylacrolein was added into the above reactor, stirred at room temperature under a nitrogen atmosphere, and the end of the reaction was detected by TLC. During the reaction process, a red precipitate gradually precipitated and was filtered with suction to obtain a crude product. Recrystallized once from absolute ethanol to obtain the red probe BNCPO with a yield of 81%. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.41 (d, J = 8.8 Hz, 4H), 7.23-7.26 (m, 2H), 6.90 (d, J = 15.6 Hz, 2H), 6.81-6.77 (m,2H), 6.75-6.69 (m, 4H), 3.02 (s, 12H), 2.87 (s, 4H). HRMS: m / z [M+H] + calcdfor [C 27 h 31 N 2 O] + 399.2436, found 399.2428.

Embodiment 2

[0026] Example 2 Fluorescence intensity of fluorescent probe BNCPO varies with viscosity.

[0027] The probe BNCPO prepared in Example 1 was dissolved in DMSO to prepare a 1 mM stock solution. Take 30 μL from the stock solution and add it to a 5 mL centrifuge tube, and use different proportions (0, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%) of glycerol An aqueous solution (pH = 7.2) was diluted to 3 mL and its fluorescence properties were measured. Single-photon fluorescence spectroscopy such as figure 2 As shown, the abscissa is the wavelength, and the ordinate is the fluorescence intensity. Depend on figure 2 It can be seen that the fluorescence intensity increases with the increase of solution viscosity. Up-converted fluorescence spectra such as image 3 As shown, the abscissa is the wavelength, and the ordinate is the fluorescence intensity. Depend on image 3 It can be seen that as the viscosity of the solution increases, the fluorescence intensity increases gr...

Embodiment 3

[0028] Example 3 Fluorescence imaging of HeLa cells by fluorescent probe BNCPO to measure viscosity.

[0029] The fluorescent probe BNCPO of the present invention is applied to HeLa cells to perform fluorescence imaging of cell viscosity, and the specific operation steps are as follows:

[0030] The Ctr group was a blank experiment, that is, HeLa cells were incubated at 37 °C for 30 min to take pictures, and the results were as follows: Figure 4 shown in a-d. At 37°C, HeLa cells were cultured for 30 min in the cell culture solution added with 10.0 μM probe BNCPO, washed three times with PBS buffer solution, and placed under a confocal fluorescence microscope for single-photon (λ ex = 488 nm) fluorescence imaging and two-photon (λ ex = 860 nm) fluorescence imaging, the results are as follows Figure 4 Shown in e-h. In the comparative experiment, 10.0 μM monensin was added to the cell culture medium with HeLa cells, incubated at 37 °C for 30 min, then incubated with 10.0...

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Abstract

The invention provides a fluorescence probe and a simple and convenient method for preparing the same. Molecules are designed, and the fluorescence probe with up-conversion properties and capability of testing the viscosity by the aid of two-photon fluorescence imaging can be synthesized. The simple and convenient method includes carrying out reaction on cyclopentanone and 4-dimethylamino allylbenzene aldehyde in organic solvents in the presence of alkali to obtain a precipitate which is the fluorescence probe. The cyclopentanone and the 4-dimethylamino allylbenzene aldehyde are used as raw materials. The fluorescence probe and the simple and convenient method have the advantages that the fluorescence probe can be applied to carrying out sensor detection on the viscosity of solution and cells, and the sensor detection includes fluorescence detection and cell imaging detection; the cell viscosity fluorescence probe is a simple, speedy and sensitive cell viscosity detection reagent, not only can be used for single-photon fluorescence measurement, but also is applicable to two-photon fluorescence measurement, and accordingly the fluorescence probe and the method have broad application prospects in the field of biological molecular detection.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting viscosity and its preparation and detection of solution and cell viscosity by methods such as spectral testing and cell imaging, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Different regions in cells have different viscosities, and cell viscosity is an important parameter to measure the viscoelastic properties of cells. When the intracellular viscosity value changes abnormally, it will affect the activity of membrane-bound proteins, inhibit insulin synthesis, etc., leading to related diseases. Traditional methods for measuring viscosity include: capillary viscometer, falling ball viscometer, rotational viscometer, etc. However, the traditional viscometer is easy to cause sample contamination, resulting in large measurement errors, and can only detect the viscosity of plasma, and cannot detect the viscosity of cell or tissue samples. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/22C09K11/06G01N21/64
CPCC07C221/00C07C225/22C09K11/06C09K2211/1007G01N21/6402G01N21/6458G01N21/6486G01N2021/6419G01N2021/6421
Inventor 林伟英戴溪
Owner UNIV OF JINAN
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